Photo by Korhan Erdol.
A fun game for any married cofounding duo is to sit in a conversation about work husbands and wives and wait. Just count down the moments until someone looks up, smiles, and says, “Well, and in your case your work spouse is your actual spouse.” And then social norms dictate that you must smile politely, as though this is the first time this particular observation has been made.
The especially fun part about this is that yes, we’re married cofounders, and yes, we worked together approximately a million years ago. But way back when we worked together the first time, we were not work besties. Neither of us was the other’s work husband or work wife or even platonic-work-soulmate. The best we can say is that we enjoyed collaborating 20 years ago and still do.
That humans need collaboration isn’t a new finding. We’re social animals. So are monkeys. And while there’s been a steady trend toward work that can be completed piecemeal and in isolation, it doesn’t change the fact that we are hard-wired for interaction. The big, expansive, long-running stuff requires sunlight and oxygen to make it go. And the longer that type of work carries on in solitude, the worse it gets. For both the work and the human.
Of the people who ask us for coffee, real or virtual, the widest-eyed are our solo practitioners. The folks who have spent too much time in the tank alone. They think big thoughts and talk themselves in circles. Tread over the same ground. And lack any counter-balance who might tell them that a project is well past ready to ship.
From this lonely workplace perspective, we seem to have stumbled on an ideal solution. Cofounders who are not only work spouses but are actual spouses. We’re quick to point out that cofounding isn’t the only way to get co-conspirators. Nor is marriage. And both are rather expensive to unwind if you find yourself in the wrong partnership. So while ours may seem like a good solve, it might not be your solve.
It turns out there’s no universal answer for keeping your head together as you build or grow a company. Some people have cofounders. Some have coaches. Some have both. And while it wasn’t our specific path, lots of people across a variety of roles and levels benefit from having a work bestie. Work besties are invaluable sounding boards. They say “yes, and” to help take your initial ideas beyond the early-nugget stage. They make your big swings bigger. And the inevitable stumbling blocks more surmountable. They cheer loudly and uncomplicatedly for your wins. And buy pad thai and cheap cava for your losses.
These people are so powerful, so impactful, and so essential, that many leaders can articulate the gap, even if they have never experienced the magic. And so it’s not surprising that, faced with this, a lot of leaders try to recreate it.
Fast alone, far together
For most leaders, the precursor to management is exceptional individual contribution. That you are badass at the IC work and clunky at the leadership bits isn’t a disqualifier, per se. It just means you need some work on your people-fu. And if you still find the human elements tricky to navigate? Don’t worry. Eventually, someone will hand you a dog-eared copy of StrengthsFinder 2.0 and say, “Just play to your strengths and have someone else handle the parts you’re no good at.”
Never mind that most skills in most workplace contexts are learnable. Never mind that a leader that can’t lead is a huge problem for the entire org. Most of all for the humans in that person’s reporting chain. But the modern workforce has a good answer for this. Or, at least, an attractive answer for this problem. Sometimes we call that person a Chief of Staff. Sometimes we call them a COO. Long ago in tech circles, people would say, “You need a Sheryl.”
That comes up less these days.
But the original dynamic-duo model is one part rounding out someone else’s gaps. And one part deliberate intermediation. When the CEO talks to anyone outside of Engineering, they quit. So, um, let’s have someone else run the all hands, k?
The shift in this model is that we’re no longer talking about a cofounder or a bestie or work spouse. You buying cava or pad thai for your peer’s bad day is adorable. You buying it for your boss’s bad day is less cute. We’ve introduced a power dynamic. And if you’ve been with us on this ride for a while, you already know. That changes everything.
Good with people
The industry and titles and seniority and pay can vary wildly, but the song is always the same.
This leader — CEO, founder, VP, department head, it doesn’t matter — is really great. No, really! They’re really smart/strategic/visionary. And once they let you in, they’re funny and even charming in their own way. But they don’t always communicate so well, or anticipate how their words will land. It’s like, you know, they can see the future of the organization so clearly and so sometimes they get impatient with folks who aren’t there yet. They just aren’t so good with people.
And that’s where you come in. You are good with people. Whatever the gig was that you thought you took, now that you’re here you function as an interpreter. You translate what they’re saying out to the broader world, yes, and also you translate what the org is saying back to them.
When you get good at it — even-handed, not self-interested or over-impressed with your own sway — the rest of the organization will reinforce your position. People start to bring you ideas to get your read on how the boss will react. People learn to bring you issues and complaints rather than tempt the impatience of your boss directly. For most people involved, your colleagues and your boss, the ride gets smoother.
But you are the shock absorber. The impatience is still a thing, the crappy communication still happens. Your flavour might be sudden changes in org direction, or questioning loyalties, or laser focus on tiny details, or chronic unavailability, or yelling. Whatever it is, it happens, and then you smooth it all over. Pull people aside. Horse-trade. You say a lot of, “I’ll talk to them.” And it mostly works. You’re good at this. We’re all happy you’re here. You hear a lot of, “I hope they’re paying you enough for this.” And maybe you get a raise.
There’s worse work out there. Like, at a minimum you’re reducing some harm, right? Your boss is doing less damage, you’re building influence, and maybe you can even sort of steer the ship towards calmer waters overall? Noble aspirations, for sure. But how do you feel? Subjectively, what’s your experience of work? What’s your experience of after-hours push notifications? How does Sunday evening feel?
And what happens you have to smooth something that shouldn’t be smoothed?
Where does the buck stop?
The thing about acting as interpreter for someone more senior is that it gives you plausible deniability by taking away agency. Like, sure, if something great happens, we all say it couldn’t have happened without you. But if your boss blows someone up, or ghosts an important meeting, or makes snap changes to the org, well, that’s not really your fault, and we all know you’re doing your best to help everyone out. Sort of a sweet deal, accountability-wise.
But it also means you insulate your boss from the consequences of their actions. Drivers drive closer to bikers wearing helmets. And, in our experience, assholes with a cleanup squad feel a freer hand than those who have to deal with the fallout themselves. When you sit in that interpreter seat, the question is always whether you’re doing harm reduction, or enabling.
Was it harm reduction, or enablement, when Linda Yaccarino agreed to run Twitter for Elon? Each time Elon re-tooled Grok to make it more hateful, who called advertisers to try to slow the exodus? Would Zuck have been able to go so fast, or break so many things, if Sheryl weren’t there to clean it up? And does it always have to end up this way? Running cover for powerful people who lack emotional maturity and intellectual honesty?
Sometimes it for sure does. But not always. The truth is that there’s no built-in red line where it tips from harm reduction to enabling. It’s always both, at the same time. If you find yourself in a role where you spend a lot of time translating, interpreting, massaging reality, message-adjusting for a more senior person, you’re doing both, too.
And really, all we want to say to you is: eyes open. Some leaders really do need that translation layer, and you might be the perfect fit for it. But if you’re doing it, let it be because you’re choosing what you enable, and pushing back on what you won’t. That second thing makes all the difference.
Like, the reason so many people find work besties helpful is because a peer can give you not only “yes, and,” they can also say, “what if, instead…,” or even, “Nope, that ain’t it.” And so can you. You can challenge each other’s thinking without fear of reprisals because there’s no implicit threat that one of you can fire the other if the relationship becomes displeasing.
The temptation is to imagine that when you work in this intermediary role, you can’t really do those things. Like you’re trapped in a deeply un-fun improv class made only of “yes, and.” Credit for the good stuff, no blame for the bad stuff, and no agency along the way. But it isn’t true. Sheryl isn’t off the hook and neither are you. Unless and until that leader learns to navigate their organization’s interpersonal dynamics directly, they need you. And you’re allowed to need things in return.
— Melissa & Johnathan
